Synthesis process of steroid compound, canrenone and spirolactone

A technology for steroid compound and synthesis process, which is applied in the field of drug synthesis, can solve the problems of poor appearance and quality of canrenone and spironolactone, difficulty in solvent recovery, and high COD in waste water, and achieves a process that is environmentally friendly, high in molar yield, and waste water. small amount of effect

Pending Publication Date: 2020-11-06
ZHEJIANG LANGHUA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] This route is simple, the reaction conditions are mild, and it is easy to scale up production, but the environment is not friendly and the pollution is relatively large. Among them, the oxygen bridge reaction and dehydrogenation reaction cause a large amount of wastewater, solvent recovery is difficult, and the COD of wastewater is high.
Similarly, the appearance and quality of canrenone and spironolactone synthesized by this route are relatively poor

Method used

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  • Synthesis process of steroid compound, canrenone and spirolactone
  • Synthesis process of steroid compound, canrenone and spirolactone
  • Synthesis process of steroid compound, canrenone and spirolactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] This embodiment provides a synthetic process for steroidal compounds, and the specific synthetic route is as follows:

[0101]

[0102] Wherein the compound shown in the formula I can be purchased from the market.

[0103] 100g of ethanol, 15.6g of sodium ethoxide, and 48.9g of diethyl malonate were added to a three-necked flask, then 50g of the compound of formula I was added, the temperature was raised to 30°C and the reaction was kept for 6 hours, and then 200ml of 5% sodium hydroxide aqueous solution was added, React at 0°C for 8 hours, add 300ml of 10% hydrochloric acid aqueous solution, react at 0°C for 24 hours, cool down, filter with suction to obtain the compound shown in formula II (R=H), and recrystallize from ethanol to obtain 54.2g of white crystals.

[0104] The relevant characterization data of the compound of formula II are as follows:

[0105] [α] 20 D =+158°(C=1,CH 2 Cl 2 ).

[0106] UVmax: 240nm.

[0107] Elemental Analysis: Theoretical Calc...

Embodiment 2

[0115]

[0116] Add 100g of ethanol, 22g of sodium ethoxide, and 62.1g of diethyl malonate into a three-necked flask, then add 50g of the compound of formula I, raise the temperature to 60°C and keep it warm for 4 hours, then add 200ml of 10% hydrochloric acid aqueous solution, and react at 60°C 0.5 hour, cooling, suction filtration, obtains the compound shown in formula II (R=C 2 h 5 ), recrystallized from ethanol to obtain 57.6 g of white crystals.

Embodiment 3

[0118]

[0119] Add 100g of ethanol, 24g of sodium ethoxide, and 55.6g of methyl ethyl malonate into a three-necked flask, then add 50g of the compound of formula I, heat up to 80°C for 6 hours, and then add 200ml of 5% aqueous sodium hydroxide solution. React at 25°C for 8 hours, add 300ml of 10% hydrochloric acid aqueous solution, heat up to 60°C and react for 0.5 hours, cool down, filter with suction to obtain the compound shown in formula II (R=H), and recrystallize from ethanol to obtain 54.4g of white crystals.

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Abstract

The invention relates to the technical field of medicine synthesis, in particular to a synthesis process of a steroid compound, canrenone and spirolactone. An embodiment of the invention provides thesteroid compound. The steroid compound has a structural formula as shown in the specification. In the structural formula, R is selected from H or an alkyl group. The steroid compound can be used for synthesizing canrenone and spirolactone, synthesis conditions are mild, synthesis efficiency is high, the amount of wastewater is small, the quality of the formed products is high, and production costcan be effectively reduced.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to the synthesis process of steroidal compounds, canrenone and spironolactone. Background technique [0002] Canrenone, the chemical name is 17β-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid-γ-lactone, used for the treatment of heart failure edema and liver cirrhosis Ascites is a commonly used diuretic and an important intermediate for the synthesis of aldosterone receptor antagonist spironolactone. [0003] Spironolactone (Spironolactone), the chemical name is 17β-hydroxy-3-oxo-7α-(acetylthio)-17α-pregna-4-ene-21-carboxylic acid-γ-lactone, which was developed by Pfizer of the United States Mineralocorticosteroid antagonists, which are now on the market in many countries, are clinically used as diuretics, also known as spirone and spironolactone. Their structure is similar to that of aldosterone, and they are competitive inhibitors of aldosterone. In addition, spiro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J21/00
CPCC07J21/003
Inventor 张帅金超余佳麟
Owner ZHEJIANG LANGHUA PHARMA
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